Oh my. This was our special NYE date meal, and though it was a spur-of-the-moment decision, it did not disappoint. From our appetizer of grilled calamari (with the suckers still on the tentacles!) to the best ravioli of my life to the 400+ wine list (all Italian!), the meal was perfect from start to finish. I just wish I hadn’t forgotten my camera!

Though the venue alone would have been by far my favorite place we visited (Miles Davis played there! It’s the definition of a classic jazz club!), the music is what made it extra special. Roy Hargrove, widely considered the best current jazz trumpeter of the day, killed it with a show that made me melt back into a time of martinis and cocktail dresses. Here’s a great review of the whole thing.

4. Walking

I adamantly feel that the best way to get to know a city is to get lost in it. Though it was a bit cold for me (read: miserable) so I didn’t explore quite as much as I’d like, the walks were the best part. We wandered into the best little diner, past the Chicago Tribune, and into a dive(ish) bar with a huge selection of local beers on tap. I’d love to go back when I can walk 1/4 of a mile without whining uncontrollably.

5. Breakfast

Orange, Ann Sather, the aforementioned diner, and an Ethiopian brunch made each morning worth walking into those bitter freezing temperatures.